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EPSRC Reference: GR/M12582/01
Title: ATROPISOMERIC AMIDES AS LIGANDS FOR ASYMMETRIC SYNTHESIS
Principal Investigator: Clayden, Professor J
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Department: Chemistry
Organisation: Victoria University of Manchester, The
Scheme: Standard Research (Pre-FEC)
Starts: 01 February 1999 Ends: 31 January 2000 Value (£): 48,919
EPSRC Research Topic Classifications:
Asymmetric Chemistry
EPSRC Industrial Sector Classifications:
No relevance to Underpinning Sectors
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Summary on Grant Application Form
New methods for the asymmetric synthesis of organic compounds, particularly those forming new C-C bonds under catalytic conditions, are vitally important for the pharmaceutical and fine chemicals industries. We aim to develop a new class of metal ligands for use in catalytic asymmetric synthesis. These ligands will be group of tertiary aromatic amides, axially chiral by virtue of conformational restriction. They offer several potential advantages, not the least being the versatility of their lithiation chemistry which will make optimisation processes simple and efficient. We will first develop methods for the synthesis of these compounds as single enentiomers, exploiting the potential of some members of the class for thermal racemisation. We propose five methods to achieve this aim: two of these methods are completely original. We will use these methods to make simple starting materials for use in the synthesis of our ligands, which we will test in the catalysis of three model reactions: additions of organozincs to carbonyl compounds, conjugate additions of lithium organocuprates to unsaturated ketones, and palladium-catalysed hydrosilylation reactions.
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